Professional Documents
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Sections 14.1-14.5
Biochemistry was developed later as the study of the chemical compounds and reactions in living cells.
Copyright Houghton Mifflin Company. All rights reserved. Intro 14 | 2
Whler was able to make urea, a carbon compound in human urine, in the laboratory from a mineral. Organic chemistry is an enormous field. In this chapter we will investigate some of the fundamental concepts.
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Section 14.1
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Two structural formulas are shown above. Which on does not represent a real compound? In structure (a) each H and halogen has one bond, each C has four bonds, and each O has two bonds. This is a valid structure.
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As we examine (b), we note that each H has one bond, each C has four bonds, the N has three bonds, BUT the O has three bonds. The O should only have two bonds. Therefore (b) is not a valid structure.
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The structural formula above appears in a recent chemistry book. Check the number of bonds to each atom and determine whether any bonding rules are violated.
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Hydrocarbons
Hydrocarbons are the most simple organic compounds. Hydrocarbons contain only carbon (C) and hydrogen. (H) For classification purposes, all other organic compounds are considered derivatives of hydrocarbons. Hydrocarbons can be divided into aromatic and aliphatic hydrocarbons.
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Classification of Hydrocarbons
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Aromatic Hydrocarbons
Aromatic hydrocarbons contain one or more benzene ring. Benzene (C6H6) is the most important aromatic hydrocarbon. It is a clear, colorless liquid with a distinct odor, and is a carcinogen (cancer-causing agent.) Traditional Lewis Structure
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Benzene
Structural Formulas and Short-hand Symbols
The Lewis structure and the Kekul symbol both indicate that the carbons in the ring have alternating double and single bonds.
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Benzene representation
Benzene representation howing a flat molecule with six delocalized electrons forming an cloud above and below the plane of the ring. Properties of the benzene molecule and advanced bonding theory indicate this structure. The six electrons appear to be shared by all the carbon atoms in the ring.
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When Other Atoms are Substituted for the Hs in the Benzene Ring
A vast array of other compounds can be produced
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From Ebbing/Gammon 7th Ed., p. 380 Copyright Houghton Mifflin Company. All rights reserved. Section 14.2 14 | 21
Cl F
1-chloro-2-fluorobenzene
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Aliphatic Hydrocarbons
Aliphatic hydrocarbons are hydrocarbons having no benzene rings. Aliphatic hydrocarbons can be divided into four major divisions:
Alkanes Cycloalkanes Alkenes Alkynes
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Classification of Hydrocarbons
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Alkanes
Alkanes are hydrocarbons that contain only single bonds. Alkanes are said to be saturated hydrocarbons
Because their hydrogen content is at a maximum.
Alkane general formula CnH2n + 2 The names of alkanes all end in -ane. Methane butane are gases Pentane C17H36 are liquids C18H38 and higher are solids
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Alkane Products
Alkanes are also found in paints, plastics, drugs, detergents, insecticides, and cosmetics.
Only 6% of the petroleum consumed goes into making these products.
The remaining 94% of the petroleum is burned as one of the various energy-related products. Although alkanes are highly combustible, they are otherwise not very reactive.
Any reaction would require the breaking of the strong CH and CC bonds.
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Alkyl Group
Alkyl group contains one less hydrogen than the corresponding alkane. In naming this group the -ane is dropped and -yl is added. For example, methane becomes methyl. Ethane becomes ethyl.
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Alkyl Group
This group does not exist independently but occurs bonded to another atom or molecule.
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Constitutional Isomers
Compounds that have the same molecular formula but different structural formulas In the case of many alkanes there is more than one way to arrange the atoms For example butane and isobutane Both of these alkanes have the molecular formula of C4H10 But their structural formula and arrangement is quite different
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Butane
Continuous-Chain or Straight-Chain Structure
Structural Formula
C4H10
Ball-and-Stick Model
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Isobutane (2-methylpropane)
Branched-chain Structure
Structural Formula
C4H10
Ball-andStick Model
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Constitutional Isomers
Constitutional Isomers may exist whenever it is possible to construct a different structural arrangement:
Using the same number and types of atoms Without violating the octet rule
In other words, the same atoms may be connected to one another in different, but valid, ways.
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Section 14.3
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Section 14.3
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The C atoms on the main chain are numbered by counting from the end of the chain nearest the substituents.
Each substituent must have a number.
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An Example to Consider
The longest continuous chain of C atoms is five Therefore this compound is a pentane derivative with an attached methyl group
Start numbering from end nearest the substituent The methyl group is in the #2 position
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2,3-dimethylhexane
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Number the C atoms from right to left. Attach two methyl groups (CH3--) to carbon number 2 and one to number 4.
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2,2,4-trimethylpentane
Ball-and-Stick Model
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Cycloalkanes
Members of the cycloalkane group possess rings of carbon atoms. They have the general formula CnH2n. Each carbon atom is bonded to a total of four carbon or hydrogen atoms. The smallest possible ring consists of cyclopropane, C3H6.
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Note that in the condensed structural formulas, there is a carbon atom at each corner and enough hydrogens are assumed to be attached to give a total of four single bonds.
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Alkenes
Members of the alkene group have a double bond between two carbon atoms. One hydrogen atom has been removed from two adjacent carbon atoms, thereby allowing the two adjacent carbon atoms to form a double bond. General formula is CnH2n Begins with ethene (ethylene) C2H4
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Naming Alkenes
-ane suffix for the corresponding alkane is changed to -ene for alkenes. A number preceding the name indicates the C atom on which the double bond starts.
The carbons are numbered such that the double bond has the lowest number.
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Alkynes
Members of the alkyne group have a triple bond between two carbon atoms. Two hydrogen atoms have been removed from each of two adjacent carbon atoms, thereby allowing the two adjacent carbon atoms to form a triple bond. General formula is CnH2n-2 Begins with ethyne (acetylene) C2H2
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Derivatives of Hydrocarbons
Organic molecule characteristics depend on the number, arrangement, and type of atoms. Functional Group any atom, group of atoms, or organization of bonds that determine specific properties of a molecule
Generally the functional group is the reactive part of the molecule. Due to the functional groups presence, certain predictable properties ensue.
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Derivatives of Hydrocarbons
Examples of functional groups include:
The double bond in alkenes & triple bond in alkynes. Cl atom, F atom, OH group, methyl (CH3 ) group.
Derivatives of hydrocarbons are organic compounds that contain atoms other than C and H.
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Alkyl Halides
Alkyl halides have the general formula RX, where X is a halogen and R is an alkyl group CFCs (chlorofluorocarbons) are examples of alkyl halides. A well known CFC is dichlorodifluoromethane (Freon-12)
Extensively used in the past in cooling devices.
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Alkyl Halides
Another example of an alkyl halide is chloroform.
In the past it was used as a surgical anesthetic but it is now a known carcenogen.
Carbon tetrachloride was also used extensively in the past, until it was linked to liver damage.
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Fill in the open bonds with H atoms and name the compounds.
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1-Fluoropropane
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2-Fluoropropane
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Alcohols
Alcohols are organic compounds containing the hydroxyl group, OH, attached to an alkyl group.
General formula is ROH
Their IUPAC (International Union of Pure and Applied Chemistry) names end in -ol. The most simple alcohol is methanol
Also called methyl alcohol or wood alcohol. (poisonous)
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Alcohols
Another common alcohol is ethanol. (CH3CH2OH)
Also known as ethyl alcohol or grain alcohol Least toxic and most important of the alcohols
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Carbohydrates
Compounds that contain multiple hydroxyl groups in their molecular structure.
Names end in -ose
Sugars, starches, and cellulose are the most important carbohydrates. Glucose (C6H12O6) and fructose (C6H12O6) are important sugars.
Note that glucose and fructose are isomers.
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Carbohydrates - Sugars
Fructose is the sweetest of all sugars and is found in fruits and honey. Glucose (also called dextrose) is found in sweet fruits, such as grapes and figs, in flowers, and in honey. Carbohydrates must be broken down into glucose for circulation in the blood.
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Carbohydrates - Starch
Starch consists of very long chains (up to 3000 units) of glucose. Produced by plants in their seeds, tubers, and fruits When these plants parts are eaten, our digestive processes covert the starches back into glucose.
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Carbohydrates - Cellulose
Cellulose is also a polymer of glucose and has the general formula (C6H10O5)n.
Slightly different structure with different properties than starches
Cell walls of plants are dominantly composed of cellulose. Humans do not have the appropriate enzymes (called cellulases) to break cellulose down. Termites and many herbivores contain bacteria that allow the breakdown of cellulose.
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Amines
Organic compounds that contain nitrogen and are basic (alkaline) are called amines. General formula for an amine is RNH2.
One or two additional alkyl groups could be attached to the N atom, in place of H atoms.
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Amines - Medicinal
Many amines have medicinal applications. Amphetamines raise the glucose level in the blood resulting in less fatigue and hunger.
These synthetic drugs certainly have legitimate medical uses, but can be addictive and lead to insomnia, excessive weight loss, and paranoia.
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The French artist David portrays The Death of Socrates due to the deadly alkaloid coniine
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Carboxylic Acids
Carboxylic acids contain the carboxyl group . (COOH) They have the general formula RCOOH.
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Carboxylic Acids
Formic acid is the simplest carboxylic acid.
This is the substance that causes the painful sting of insect bites.
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Esters
Ester a compound that has the following general formula RCOOR In the general formula for an ester the R and R can be any alkyl group.
Although R and R can be identical, they are usually different.
Odors of Esters
Natural flavors are generally complex mixtures of esters and other constituents
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Formation of an Ester
Ester formation the reaction of a carboxylic acid and an alcohol give an ester and water
Heat is required and sulfuric acid is a catalyst.
Note, in this reaction that the OH from the carboxylic acid unites with the H from the alcohol to form H2O. The remaining two fragments bond together to form the ester.
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From Ebbing, General Chemistry, 6th Ed. Copyright Houghton Mifflin Company. All rights reserved. Section 14.4 14 | 88
Fats
Fats are a type of ester formed by the combination of the trialcohol named glycerol and fatty acids.
Glycerol is CH2(OH)CH(OH)CH2(OH) Stearic Acid (C17H35COOH) is found in beef fat, and is a typical fatty acid.
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Fats
Generally fats from animals are solid at room temperature. Fats from plants and fish are generally liquid at room temperature. Liquid fats are referred to as oils.
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Hydrogenation
Liquid fats contain double bonds between some of the carbon atoms.
These liquids fats are termed unsaturated.
Hydrogenation is the process of adding H to the C atoms that have a double bond.
The hydrocarbon chains become saturated or nearly saturated and the liquid fat is changed to a solid.
Hydrogenation
When Cottonseed Oil (liquid) is hydrogenated, Margarine (solid) is the result.
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Soaps
Soap the sodium slats of fatty acids Soap is formed by reacting a fat with sodium hydroxide (NaOH, lye.) The ester bonds break giving rise to glycerol and sodium salts of the fatty acids. Sodium stearate is a typical soap.
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The long nonpolar chains of the detergent molecule dissolve the grease.
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Amides
Amides are nitrogen-containing organic compounds with the general formula RCONHR.
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Amide Formation
Amide formation is similar to ester formation. A carboxylic acid reacts with an amine to form water and an amide, as shown below.
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Amino Acid
Amino acids are organic compounds that contain both an amino and carboxyl group. Glycine and alanine are the simplest amino acids. Proteins are extremely long polyamides, formed by the condensation of amino acids.
Proteins can range from a few thousand formula units (insulin) to several million formula units. Proteins serve as both structural components and enzymes.
Synthetics
Attempts to duplicate nature have long been a goal of chemists. Basic formulas and structures became known as the science of chemistry progressed. As attempts were made to synthesize natural compounds, synthetic compounds were created. Synthetics are materials whose molecules have no duplicate in nature.
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Synthetic Polymers
The first synthetic polymer was prepared by Leo Baekeland in 1907. Commercially this substance was used as an electrical insulator, called Bakelite. Chemists soon discovered that only slight substitutions to a molecule could create new substances with very different properties.
Knowing the chemical properties of the original molecules and the substitutes allowed chemists to predict the resulting properties.
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Synthetic Polymers
Due to the scientific approach, chemists were able to tailor new molecules for specific purposes. Plastics are probably the best known of this group of synthetic polymers. They can be molded and hardened for many different purposes.
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Synthetic Polymers
A polymer is a compound of very high formula mass whose long chain molecules are made of repeating units. Monomer is the fundamental repeating unit of a polymer. There are two major types of polymers:
Addition polymers Condensation polymers
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Addition Polymers
Addition polymers are formed when molecules of an alkene monomer add to one another. Recall that alkenes have a double bond between two carbon atoms. Under the proper reaction conditions the double bond opens up and attaches itself by single bonds to two other monomer molecules. Each of these monomers will then in turn attach to another monomer, and so on and on
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Polymerization of Ethene
The subscripted n on polyethylene indicates that the unit shown in brackets is repeated thousands of times. Polyethylene is the simplest of the synthetic polymers.
It is significantly inert chemically and is used to make containers.
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Teflon
Teflon is made by the polymerization of tetrafluoroethene. This polymer is a hard, strong, chemically resistant compound with a high melting point and very low surface friction.
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Condensation Polymers
Condensation polymers are formed from molecules of two or more reactive groups.
Water is the other product, hence the name condensation polymers.
Polyethylene terephthalate (PET) is formed from the polymerization of tetephthalic acid and ethylene glycol.
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Velcro
Velcro is a popular fastener made of nylon. The hooks of one surface entangle the loops of the other surface.
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